NP-MRD: Showing NP-Card for 3-O-Acetyl-beta-boswellic acid (NP0137447)

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Record Information

Version

2.0

Created at

2022-05-30 16:52:44 UTC

Updated at

2022-05-30 16:52:44 UTC

NP-MRD ID

NP0137447

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-O-Acetyl-beta-boswellic acid

Description

Beta-Boswellic acid acetate, also known as b-boswellate acetate or β-boswellic acid acetic acid, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Beta-Boswellic acid acetate is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, beta-Boswellic acid acetate has been detected, but not quantified in, alcoholic beverages and herbs and spices. 3-O-Acetyl-beta-boswellic acid is found in Boswellia sacra and Boswellia serrata. This could make beta-boswellic acid acetate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308162D          

 36 40  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 05061308162D          

 36 40  0  0  0  0            999 V2000
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    8.1575   -2.7830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3404    0.3239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9127   -0.9135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7693   -0.5011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4838   -0.9136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6272   -2.1511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4851   -2.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9700   -2.6397    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8753   -3.5583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0561   -2.1510    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 12  1  0  0  0  0
 18 17  1  0  0  0  0
 19  1  1  0  0  0  0
 19 11  1  0  0  0  0
 20  2  1  0  0  0  0
 20 19  1  0  0  0  0
 21  3  1  0  0  0  0
 22  9  2  0  0  0  0
 23 10  1  0  0  0  0
 24 12  1  0  0  0  0
 25 13  1  0  0  0  0
 26 20  1  0  0  0  0
 26 22  1  0  0  0  0
 28  4  1  0  0  0  0
 28 14  1  0  0  0  0
 28 17  1  0  0  0  0
 28 26  1  0  0  0  0
 29  5  1  0  0  0  0
 29 15  1  0  0  0  0
 29 23  1  0  0  0  0
 29 24  1  0  0  0  0
 30  6  1  0  0  0  0
 30 18  1  0  0  0  0
 30 22  1  0  0  0  0
 31  7  1  0  0  0  0
 31 16  1  0  0  0  0
 31 23  1  0  0  0  0
 31 30  1  0  0  0  0
 32  8  1  0  0  0  0
 32 24  1  0  0  0  0
 32 25  1  0  0  0  0
 32 27  1  0  0  0  0
 33 21  2  0  0  0  0
 34 27  2  0  0  0  0
 35 27  1  0  0  0  0
 36 21  1  0  0  0  0
 36 25  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0137447

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(OC(C)=O)C(C)(C5CCC34C)C(O)=O)C2C1C

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O4/c1-19-11-14-28(4)17-18-30(6)22(26(28)20(19)2)9-10-23-29(5)15-13-25(36-21(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)

> <INCHI_KEY>
YJBVHJIKNLBFDX-UHFFFAOYSA-N

> <FORMULA>
C32H50O4

> <MOLECULAR_WEIGHT>
498.737

> <EXACT_MASS>
498.370910088

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
59.72609723898214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

> <ALOGPS_LOGP>
7.17

> <JCHEM_LOGP>
7.022930819999999

> <ALOGPS_LOGS>
-6.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.467296716902504

> <JCHEM_PKA_STRONGEST_BASIC>
-7.0049333117820245

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
142.84949999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.04e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       6.235   5.225   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.903   3.685   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      18.238  -1.705   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.902  -0.165   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.904  -0.165   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.903  -2.475   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.235  -0.489   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.248  -5.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.236   1.375   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.570   0.605   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.902   2.915   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.570  -4.015   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.571  -1.705   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.902   1.375   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.237  -0.935   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.236  -3.245   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.235  -0.935   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.569  -1.705   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.235   3.685   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.569   2.915   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      18.238  -3.245   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.903   0.605   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.570  -0.935   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      12.904  -3.245   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.571  -3.245   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.569   1.375   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      15.227  -5.195   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.235   0.605   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.904  -1.705   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.903  -0.935   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      10.236  -1.705   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      14.237  -4.015   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      19.572  -4.015   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      16.744  -4.927   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      14.701  -6.642   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      16.905  -4.015   0.000  0.00  0.00           O+0
CONECT    1   19                                                            
CONECT    2   20                                                            
CONECT    3   21                                                            
CONECT    4   28                                                            
CONECT    5   29                                                            
CONECT    6   30                                                            
CONECT    7   31                                                            
CONECT    8   32                                                            
CONECT    9   10   22                                                       
CONECT   10    9   23                                                       
CONECT   11   14   19                                                       
CONECT   12   16   24                                                       
CONECT   13   15   25                                                       
CONECT   14   11   28                                                       
CONECT   15   13   29                                                       
CONECT   16   12   31                                                       
CONECT   17   18   28                                                       
CONECT   18   17   30                                                       
CONECT   19    1   11   20                                                  
CONECT   20    2   19   26                                                  
CONECT   21    3   33   36                                                  
CONECT   22    9   26   30                                                  
CONECT   23   10   29   31                                                  
CONECT   24   12   29   32                                                  
CONECT   25   13   32   36                                                  
CONECT   26   20   22   28                                                  
CONECT   27   32   34   35                                                  
CONECT   28    4   14   17   26                                             
CONECT   29    5   15   23   24                                             
CONECT   30    6   18   22   31                                             
CONECT   31    7   16   23   30                                             
CONECT   32    8   24   25   27                                             
CONECT   33   21                                                            
CONECT   34   27                                                            
CONECT   35   27                                                            
CONECT   36   21   25                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
b-Boswellate acetate	Generator
b-Boswellic acid acetic acid	Generator
beta-Boswellate acetate	Generator
beta-Boswellic acid acetic acid	Generator
Β-boswellate acetate	Generator
Β-boswellic acid acetic acid	Generator
3-(Acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylate	Generator
3-O-Acetyl-beta-boswellic acid	MeSH
Acetyl-beta-boswellic acid	MeSH

Chemical Formula

C₃₂H₅₀O₄

Average Mass

498.7370 Da

Monoisotopic Mass

498.37091 Da

IUPAC Name

3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4-carboxylic acid

Traditional Name

3-(acetyloxy)-4,6a,6b,8a,11,12,14b-heptamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1H-picene-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1CCC2(C)CCC3(C)C(=CCC4C5(C)CCC(OC(C)=O)C(C)(C5CCC34C)C(O)=O)C2C1C

InChI Identifier

InChI=1S/C32H50O4/c1-19-11-14-28(4)17-18-30(6)22(26(28)20(19)2)9-10-23-29(5)15-13-25(36-21(3)33)32(8,27(34)35)24(29)12-16-31(23,30)7/h9,19-20,23-26H,10-18H2,1-8H3,(H,34,35)

InChI Key

YJBVHJIKNLBFDX-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Boswellia sacra	LOTUS Database	35616633
Boswellia serrata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Hydroxysteroid
15-hydroxysteroid
Steroid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.17	ALOGPS
logP	7.02	ChemAxon
logS	-6.7	ALOGPS
pKa (Strongest Acidic)	4.47	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	142.85 m³·mol⁻¹	ChemAxon
Polarizability	59.73 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0035160

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013797

KNApSAcK ID

Not Available

Chemspider ID

3006422

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3778105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3-O-Acetyl-beta-boswellic acid (NP0137447)

MOL for NP0137447 (3-O-Acetyl-beta-boswellic acid)

3D MOL for NP0137447 (3-O-Acetyl-beta-boswellic acid)

3D SDF for NP0137447 (3-O-Acetyl-beta-boswellic acid)

3D-SDF for NP0137447 (3-O-Acetyl-beta-boswellic acid)

PDB for NP0137447 (3-O-Acetyl-beta-boswellic acid)

3D PDB for NP0137447 (3-O-Acetyl-beta-boswellic acid)

SMILES for NP0137447 (3-O-Acetyl-beta-boswellic acid)

INCHI for NP0137447 (3-O-Acetyl-beta-boswellic acid)

Structure for NP0137447 (3-O-Acetyl-beta-boswellic acid)

3D Structure for NP0137447 (3-O-Acetyl-beta-boswellic acid)